I live in WI and did exactly what you were talking about during 2009. I graduated in the WORST part of the recession, there were literally 7 junior ID positions posted that entire fucking year on Coroflot.
What I did was setup my own LLC, which I used to write off expenses like my laptop, gas, travel expenses, meals with clients, portfolio printing, business cards, the usual.
Then I freelanced about 20 hours a week, while applying for about 5-10 jobs a week that were SORT OF in my field. I then applied for unemployment, and was accepted.
I got a phone call from the unemployment office, explained that I am actively seeking a full time position, but am currently running an LLC to make ends meet until I find full time employment. I also told him I am not working 40 hours a week, and I do not have benefits of any kind. He said that I was not eligible for unemployment checks. I argued with him, asking why, as I know other people who are doing exactly what I was doing. He said he’d call me back, and he did, and said everything was fine. Also, keep in mind, even if you make $1500 in one week of freelancing, THAT IS NOT YOUR MONEY. That money is your LLC’s money, which is owned by you, but it’s own company. You can STILL collect your FULL unemployment check despite what you make that week for your company. Again, you are running an LLC purely to help support yourself WHILE YOU ARE LOOKING FOR A JOB.
Overall, it was a good move. I made about 18k in freelancing that summer, and about 4-6k in unemployment that year. I was BARELY able to support myself, but was then able to secure a full time position. Do it. I’d rather you get unemployment while looking than take some crappy job washing dishes or politicians bailing out some gigantic company that’s made stupid decisions for 4 decades (cough GM cough).